4,8-Dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one used as perfumes

ABSTRACT

The use of 4,8-dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one as fragrances with a rose odour is described. Corresponding perfume compositions, perfumed products and processes for producing or strengthening a rose odour are also described.

The present invention relates to the use of 4,8-dimethyl-7-nonen-2-one,4,8-dimethylnonan-2-one or a mixture of these compounds as fragrances.

There is a general need for rose fragrances in the perfume industrybecause consumers are constantly looking for new and modern rose-scentedperfumes. Fragrances with a rose odour are used in large quantities andinnumerable variations in perfumes, mixtures of fragrances (perfumecompositions) and perfume formulations for a very wide variety of fieldsof application.

The known rose fragrances include the compounds geraniol(3,7-dimethyl-2,6-octadien-1-ol) and citronellol(3,7-dimethyl-2-octen-1-ol), but it has now emerged that many peoplehave intolerance reactions, e.g. allergic reactions, to these compounds.

The perfume industry therefore has not only a general need for otherrose fragrances, but also a specific need for rose fragrances that donot possess said negative toxicological properties and areadvantageously capable of replacing the rose fragrances geraniol andcitronellol commonly used hitherto in perfume compositions.

The object of the present invention was to provide rose fragrances whichmatch said profile of requirements. The search for suitable rosefragrances that led to the present invention was complicated by thefollowing facts:

-   -   The mechanisms of odour perception are not sufficiently well        known.    -   The relationships between the specific odour perception, on the        one hand, and the chemical structure of the corresponding        fragrance, on the other, have not been adequately researched.    -   Even very slight changes in the structural composition of a        known fragrance frequently cause major changes in the sensory        properties and impair the human organism's tolerance.

The success of the search for suitable rose fragrances therefore dependssubstantially on intuition.

It has now been found, surprisingly, that the compounds4,8-dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one are suitable forachieving the aforesaid object.

The two compounds mentioned each have a rose-like odour and propertiesin application technology which enable them to be used in perfumecompositions in place of the conventional (but allergenic) rosefragrances geraniol and citronellol. The match between the olfactoryprofiles of geraniol and citronellol, on the one hand, and4,8-dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one, on the other, issurprising because the latter compounds are not primary alcohols butketones, i.e. substances with a functionality very different from thatof primary alcohols. Normally, such substantial differences in thefunctional groups of compounds lead to very different sensoryproperties, even if they are otherwise structurally similar.

There has so far been no sensory description of the compound4,8-dimethylnonan-2-one. Although an olfactory description of thecompound 4,8-dimethyl-7-nonen-2-one has been disclosed in IndianPerfumer 22 (4), pages 225-228 (1978), it reads: “coconut, rose-like”,so it had to be assumed that 4,8-dimethyl-7-nonen-2-one is not suitableas a substitute for geraniol and citronellol, because although thedisclosure in Indian Perfumer confirms a rose-like olfactory character,this observation was coupled with the further observation that a primarycoconut-like odour is present. Our own experiments have now shown,surprisingly, that the olfactory description given in Indian Perfumer isnot correct. In fact, a coconut-like odour cannot be observed in thesensory examination of 4,8-dimethyl-7-nonen-2-one; rather, the compoundhas a radiantly rose-like, fruity, natural odour reminiscent of tearoses and for this very reason is outstandingly suitable as a substitutefor geraniol and citronellol. The same applies to the compound4,8-dimethylnonan-2-one, which has a freshly citronellol-like, rose-likeodour reminiscent of citronellol oil.

The present invention relates especially to the use of4,8-dimethyl-7-nonen-2-one, 4,8-dimethylnonan-2-one or a mixture ofthese compounds for imparting a rose odour that is not accompanied by acoconut olfactory note. In particular, said compounds or mixturesthereof can be used to prepare a perfume composition with a rose odourthat is not accompanied by a coconut olfactory note.

In respect of 4,8-dimethylnonan-2-one, however, the invention alsorelates quite generally to its use as a fragrance.

Interestingly, in contrast to the compounds 4,8-dimethyl-7-nonen-2-oneand 4,8-dimethylnonan-2-one, the corresponding α,β-unsaturated ketone,4,8-dimethyl-3,7-nonadien-2-one, has more of a citrus-like odour thatdoes not qualify it as a substitute for geraniol and citronellol.

The present invention further relates to perfume compositions with arose odour, comprising

-   -   an organoleptically effective amount of        4,8-dimethyl-7-nonen-2-one, 4,8-dimethylnonan-2-one or a mixture        of these compounds        and    -   at least one other fragrance.

The other fragrance(s) can be selected especially from the followinggroups I and II, of which group I comprises rose fragrances in thenarrower sense, whereas group II comprises substances which do notthemselves have a rose note but give good effects in rose combinations,e.g. vanillin and the like, and musk fragrances. Compounds having asensitizing/allergizing effect, and natural products containing suchcompounds, are underlined in groups I and II. The use of these compoundsis less preferred.

Group I:

geranyl formate; geranyl acetate; geranyl propionate; geranylisobutyrate; geranyl butyrate; geranyl isovalerate; geranyl tiglate;geranyl benzoate; citronellyl formate; citronellyl acetate; citronellylpropionate; citronellyl isobutyrate; citronellyl butyrate; citronellylisovalerate; citronellyl tiglate; citronellyl benzoate; phenylethylalcohol; phenylacetaldehyde; phenylacetaldehyde dimethyl acetal;phenylethyl formate; phenylethyl acetate; phenylethyl propionate;phenylethyl isobutyrate; phenylethyl butyrate; phenylethyl pivalate;phenylethyl isovalerate; phenylethyl 2-ethylbutyrate; phenylethyltiglate; phenylethyl benzoate; phenylethylphenyl acetate; 2-phenoxyethylisobutyrate; geranyl methyl ether; rose oxide; phenylethyl methyl ether;phenylethyl ethyl ether; phenylethyl isoamyl ether; 2-methoxybenzylethyl ether; α-trichloromethylbenzyl acetate;α,3,3-trimethylcyclohexanemethyl acetate;2,4,6-trimethyl-3-cyclohexenemethanol; 2-ethylhexanoic acidN,N-diethylamide; 3,7-dimethyloctanol; geranylacetone; linalool;3,7-dimethyl-1,6-nonadien-3-ol; nerolidol; farnesol; 9-decenol;9-decenyl acetate; decanal; 10-undecanal; 10-undecenol;citronellyloxyacetaldehyde; 3,7-dimethyloctanylacetaldehyde;2-methyl-5-phenylpentanol; 2-methyl-5-phenylpentanal;3-methyl-5-phenylpentanol; benzophenone; diphenyl ether;diphenylmethane; α-damascone; β-damascone; δ-damascone; γ-damascone;β-damascenone; 1-(2,4,4-trimethyl-2-cyclohexenyl)-2-buten-1-one; roseoil; rose absolute; geranium oil.

Group II:

palmarosa oil; lemon oil; patchouli oil; clove oil; ylang-ylang oil;jasmine absolute; ethyl 2,3,6-trimethylcyclohexyl carbonate; hexanal;heptanal; octanal; nonanal; hexanol; heptanol; octanol; nonanol;decanol; undecanol; dodecanol; hexyl acetate; heptyl acetate; octylacetate; nonyl acetate; decyl acetate; undecyl acetate; dodecyl acetate;benzyl acetate; benzyl butyrate; benzyl benzoate; methylphenyl acetate;ethylphenyl acetate; alpha-terpineol;4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin;4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxin; ethyl2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; ethyl2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; ethyl safranate; methyl6,6-dimethyl-2-methylenecyclohexanecarboxylate; eugenol; isoeugenol;lavender oil; guaiacum wood oil; alpha-ionone; beta-ionone; cinnamylalcohol; 3-phenylpropanol; cinnamyl acetate; 3-phenylpropyl acetate;alpha-irone; cis-3-hexenol; cis-3-hexenyl acetate; cis-3-hexenylisobutyrate; vanillin; ethylvanillin; heliotropin; coumarin; ambrinol;indole; 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan;5-cyclohexadecen-1-one;6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone;8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone;cyclohexadecanone.

Normally, not only one other fragrance is present, but two, three ormore other fragrances.

As already mentioned, the compounds 4,8-dimethyl-7-nonen-2-one and4,8-dimethylnonan-2-one and mixtures thereof are particularly suitablefor creating perfume compositions with a dominant rose odour.Accordingly, the at least one other fragrance is preferably alsoselected from the group of fragrances with a rose odour. Examples ofsuch fragrances with a rose odour are those of group I above.

Of course, it is also the case in this context that conventionally notonly one other rose fragrance is used, but two, three or more.

The compounds 4,8-dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-onehave a negligible allergenic potential. Accordingly, it is normallyadvantageous not to combine them in perfume compositions with fragrancesthat do possess allergenic properties. Conventionally, therefore, aperfume composition according to the invention will not comprise anyfragrances from the following group of compounds of known allergenicpotential. However, the underlined compounds represent a particularexception here as they are rose fragrances and their use, especially insmall amounts, appears to be tolerable in some cases on account of theirparticular olfactory properties (also see above):

amylcinnamaldehyde, amylcinnamyl alcohol, anisyl alcohol, benzaldehyde,benzyl alcohol, benzyl benzoate, benzyl cinnamate, benzyl salicylate,citral, citronellol, coumarin, eugenol, farnesol, geraniol,hexylcinnamaldehyde, hydroxycitronellal, isoeugenol, lilial, limonene,linalool, lyral, methyl heptynecarbonate, methylionone, methyloctynecarbonate, cinnamaldehyde, cinnamyl alcohol, and natural productssuch as ethereal oils or other extracts containing these compounds in aneffective amount.

Surprisingly, the compounds 4,8-dimethyl-7-nonen-2-one and4,8-dimethylnonan-2-one and mixtures thereof are capable of modifyingthe olfactory properties of a mixture of the other constituents of theperfume composition to the extent that the composition acquires morebody, particularly in the top note, the rose-like naturalness and thefresh-flowery note being distinctly strengthened. The mixtures aremarkedly harmonized by their soft rose/geranium-like character,fresh-green top notes, in particular, being aesthetically incorporatedinto the composition. The slightly citrus-like olfactory aspects of4,8-dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one, somewhatreminiscent of lemon, which although not dominant are neverthelessimportant, are additionally such that the olfactory character of manycompositions is lightened and thus has a tangier and livelier effect.

The proportion of 4,8-dimethyl-7-nonen-2-one, 4,8-dimethylnonan-2-one ormixtures thereof in a perfume composition can be varied within widelimits. It conventionally ranges from 0.1 to 90 wt. %, butadvantageously from 0.5 to 70 wt. %, based in each case on the totalweight of the perfume composition.

The present invention further relates to a perfumed product comprising aperfume composition according to the invention.

Finally, the invention further relates to a process for producing a roseodour or strengthening the rose odour of a perfume composition orperfumed product, the rose odour not being accompanied by a coconutolfactory note. In the process a sensorially effective amount of4,8-dimethyl-7-nonen-2-one, 4,8-dimethylnonan-2-one or a mixture ofthese compounds is mixed with the other constituents of the perfumecomposition or added to the product.

Preferred embodiments of the uses, perfume compositions, perfumedproducts and processes according to the invention can be found in thefollowing explanations, the Examples and the attached Claims. It isunderstood that preferred forms mentioned for the perfume compositionaccording to the invention also apply correspondingly to perfumedproducts according to the invention and to uses and processes accordingto the invention.

The compounds 4,8-dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one canbe prepared by the selective hydrogenation of4,8-dimethyl-3,7-nonadien-2-one. An appropriate choice of hydrogenationconditions makes it possible selectively to prepare firstly4,8-dimethyl-7-nonen-2-one and then, by further hydrogenation,4,8-dimethylnonan-2-one. The 4,8-dimethyl-3,7-nonadien-2-one used asstarting material can be prepared according to the instructions givene.g. in DE 2256347 C3 and DE 19961030 A1.

Examples of suitable hydrogenation catalysts for the selectivehydrogenation are Raney nickel and palladium-on-charcoal. The ratio ofcatalyst to substrate will advantageously be between 0.005:1 and 0.1:1,the preferred ratio ranging between 0.01:1 and 0.0:1. The hydrogenationtemperature preferably ranges between 0 and 50° C., the particularlypreferred range being 20-40° C. The hydrogen pressure in the selectivehydrogenation is advantageously between 1 and 150 bar, the preferredrange being between 1 and 40 bar. The hydrogenation can be carried outwithout a solvent or in the presence of a suitable solvent.

On account of their aforesaid sensory properties, the ketones4,8-dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one are outstandinglysuitable for use in perfume compositions. As already mentioned, they canbe used as individual substances or in combinations with one another ina large number of products. It is particularly advantageous to combinethem with other fragrances in different, varying proportions to formnovel perfume compositions.

Even in small doses, the compounds 4,8-dimethyl-7-nonen-2-one and4,8-dimethylnonan-2-one are capable of achieving effects of pronouncednaturalness, the overall olfactory impression being strengthened andharmonized and the emanation and diffusivity being perceptivelyincreased. It is particularly surprising here that the compounds on theone hand have a strengthening effect in the direction offreshness/radiance, but on the other hand also have a harmonizingeffect.

Examples of preferred fragrances with which the compounds4,8-dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one can be combinedhave already been mentioned above. Other fragrances which are quitegenerally suitable for combination can be found e.g. in S. Arctander,Perfume and Flavor Materials, Vol. I and II, Montclair, N. J., 1969,Selbstverlag or K. Bauer, D. Garbe and H. Surburg, Common Fragrance andFlavor Materials, 4th Ed., Wiley-VCH, Weinheim 2001. The following maybe specifically mentioned:

extracts of natural raw materials, such as ethereal oils, concrete oils,absolute essences, resins, resinoids, balsams, tinctures, e.g.:

ambergris tincture; amyris oil; angelica seed oil; angelica root oil;anise oil; baldrian oil; basil oil; tree moss absolute; bay oil; mugwortoil; benzoin resin; bergamot oil; beeswax absolute; birch tar oil;bitter almond oil; savory oil; buchu leaf oil; cabreuva oil; cade oil;calmus oil; camphor oil; cananga oil; cardamom oil; cascarilla oil;cassia oil; cassia absolute; castoreum absolute; cedar leaf oil;cedarwood oil; cistus oil; citronella oil; lemon oil; copaiva balsam;copaiva balsam oil; coriander oil; costus root oil; cumin oil; cypressoil; davana oil; dill oil; dill seed oil; eau de brouts absolute; oakmoss absolute; elemi oil; tarragon oil; eucalyptus citriodora oil;eucalyptus oil; fennel oil; pine needle oil; galbanum oil; galbanumresin; geranium oil; grapefruit oil; guaiacum wood oil; gurjun balsam;gurjun balsam oil; helichrysum absolute; helichrysum oil; ginger oil;iris root absolute; iris root oil; jasmine absolute; calamus oil; bluecamomile oil; Roman camomile oil; carrot seed oil; cascarilla oil;Scotch fir oil; spearmint oil; caraway oil; ladanum oil; ladanumabsolute; ladanum resin; lavandin absolute; lavandin oil; lavenderabsolute; lavender oil; lemongrass oil; lovage oil; distilled lime oil;pressed lime oil; linaloa oil; litsea cubeba oil; laurel leaf oil; maceoil; majoram oil; mandarin oil; massoi bark oil; mimosa absolute;ambrette oil; musk tincture; muscatel sage oil; nutmeg oil; myrrhabsolute; myrrh oil; myrtle oil; clove leaf oil; clove blossom oil;neroli oil; frankincense absolute; frankincense oil; opopanax oil;orange blossom absolute; orange oil; oreganum oil; palmarosa oil;patchouli oil; perilla oil; Peruvian balsam oil; parsley leaf oil;parsley seed oil; petitgrain oil; peppermint oil; pepper oil; pimentooil; pine oil; European pennyroyal oil; rose absolute; rosewood oil;rose oil; rosemary oil; Dalmatian sage oil; Spanish sage oil; sandalwoodoil; celery seed oil; lavender spike oil; Japanese anise oil; styraxoil; tagetes oil; fir needle oil; tea tree oil; turpentine oil; thymianoil; tolu balsam; tonka absolute; tuberose absolute; vanilla extract;violet leaf absolute; verbena oil; vetiver oil; juniper oil; wine yeastoil; wormwood oil; wintergreen oil; ylang oil; hyssop oil; civetabsolute; cinnamon leaf oil; cinnamon bark oil; and fractions thereof oringredients isolated therefrom.

If said substances include compounds with sensitizing/allergizingproperties, the above remarks apply correspondingly.

individual fragrances from the following groups:

hydrocarbons, e.g. 3-carene; α-pinene; β-pinene; α-terpinene;γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene;farnesene; limonene; longifolene; myrcene; ocimene; valencene;(E,Z)-1,3,5-undecatriene; styrene; diphenylmethane;

aliphatic alcohols, e.g. hexanol; octanol; 3-octanol;2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol;(E)-2-hexenol; (E)- and (Z)-3-hexenol; 1-octen-3-ol; mixture of3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E,Z)-2,6-nonadienol;3,7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol;4-methyl-3-decen-5-ol;

aliphatic aldehydes and their acetals, e.g. hexanal; heptanal; octanal;nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal;2-methylnonanal; (E)-2-hexenal; (Z)-4-heptenal; 2,6-dimethyl-5-heptenal;10-undecenal; (E)-4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal;2,6,10-trimethyl-5,9-undecadienal; heptanal diethyl acetal;1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde;1-(1-methoxypropoxy)-(E/Z)-3-hexene;

aliphatic ketones and their oximes, e.g. 2-heptanone; 2-octanone;3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanoneoxime; 2,4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;

aliphatic sulfur-containing compounds, e.g. 3-methyl-thiohexanol;3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate;3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol;

aliphatic nitriles, e.g. 2-nonenoic acid nitrile; 2-undecenoic acidnitrile; 2-tridecenoic acid nitrile; 3,12-tridecadienoic acid nitrile;3,7-dimethyl-2,6-octadienoic acid nitrile; 3,7-dimethyl-6-octenoic acidnitrile;

esters of aliphatic carboxylic acids, e.g. (E)- and (Z)-3-hexenylformate; ethyl acetoacetate; isoamyl acetate; hexyl acetate;3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E)-2-hexenylacetate; (E)- and (Z)-3-hexenyl acetate; octyl acetate; 3-octyl acetate;1-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate;hexyl butyrate; (E)- and (Z)-3-hexenyl isobutyrate; hexyl crotonate;ethyl isovalerate; ethyl 2-methylpentanoate; ethyl hexanoate; allylhexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; ethyl(E,Z)-2,4-decadienoate; methyl 2-octynate; methyl 2-nonynate; allyl2-isoamyloxyacetate; methyl 3,7-dimethyl-2,6-octadienoate;4-methyl-2-pentyl crotonate;

acyclic terpene alcohols, e.g. citronellol; geraniol; nerol; linalool;lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol;2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-2-ol;2-methyl-6-methylen-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol;2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl-4,6-octadien-3-ol;3,7-dimethyl-1,5,7-octatrien-3-ol; 2,6-dimethyl-2,5,7-octatrien-1-ol;and their formates, acetates, propionates, isobutyrates, butyrates,isovalerates, pentanoates, hexanoates, crotonates, tiglates,3-methyl-2-butenoates;

acyclic terpene aldehydes and ketones, e.g. geranial; neral;citronellal; 7-hydroxy-3,7-dimethyloctanal;7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal;geranylacetone; and the dimethyl and diethyl acetals of geranial, neral,7-hydroxy-3,7-dimethyloctanal;

cyclic terpene alcohols, e.g. menthol; isopulegol; alpha-terpineol;terpinen-4-ol; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol;isoborneol; linalool oxide; nopol; cedrol; ambrinol; vetiverol; guaiol;and their formates, acetates, propionates, isobutyrates, butyrates,isovalerates, pentanoates, hexanoates, crotonates, tiglates,3-methyl-2-butenoates;

cyclic terpene aldehydes and ketones, e.g. menthone; isomenthone;8-mercaptomenthan-3-one; carvone; camphor; fenchone; alpha-ionone;beta-ionone; alpha-n-methylionone; beta-n-methylionone;alpha-isomethylionone; beta-isomethylionone; alpha-irone;alpha-damascone; beta-damascone; beta-damascenone; delta-damascone;gamma-damascone; 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one;1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8(5H)-one;2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; nootkatone;dihydronootkatone; 4,6,8-megastigmatrien-3-one; alpha-sinensal;beta-sinensal; acetylated cedarwood oil (methyl cedryl ketone);

cyclic alcohols, e.g. 4-tert-butylcyclohexanol;3,3,5-trimethylcyclohexanol; 3-isocamphylcyclohexanol;2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol;2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

cycloaliphatic alcohols, e.g. alpha-3,3-trimethylcyclohexylmethanol;1-(4-isopropylcyclohexyl)ethanol;2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol;2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol;2-ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol;3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)pentan-2-ol;3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol;3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol;1-(2,2,6-trimethylcyclohexyl)pentan-3-ol;1-(2,2,6-tri-methylcyclohexyl)hexan-3-ol;

cyclic and cycloaliphatic ethers, e.g. cineol; cedryl methyl ether;cyclododecyl methyl ether; 1,1-dimethoxycyclododecane;(ethoxymethoxy)cyclododecane; alpha-cedrene epoxide;3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]-furan;3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]-furan;1,5,9-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene; rose oxide;2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane;

cyclic and macrocyclic ketones, e.g. 4-tert-butyl-cyclohexanone;2,2,5-trimethyl-5-pentylcyclopentanone*; 2-heptylcyclopentanone*;2-pentylcyclopentanone*; 2-hydroxy-3-methyl-2-cyclopenten-1-one;3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one;3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone;3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone;4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone;4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one;6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone;8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone;cyclohexadecanone;

cycloaliphatic aldehydes, e.g. 2,4-dimethyl-3-cyclohexenecarbaldehyde;2-methyl-4-(2,2,6-trimethylcyclohexen-1-yl)-2-butenal;4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde;4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde;

cycloaliphatic ketones, e.g. 1-(3,3-dimethylcyclohexyl)-4-penten-1-one;2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone;1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one;2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methylketone; methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone;tert-butyl 2,4-dimethyl-3-cyclohexen-1-yl ketone;

esters of cyclic alcohols, e.g. 2-tert-butylcyclohexyl acetate;4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate;4-tert-pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate;decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate;3-pentyltetrahydro-2H-pyran-4-yl acetate;decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5- or 6-indenyl acetate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5- or 6-indenyl propionate;4,7-methano-3a,4,5,6,7,7a-hexahydro-5- or 6-indenyl isobutyrate;4,7-methanooctahydro-5- or 6-indenyl acetate;

esters of cycloaliphatic alcohols, e.g. 1-cyclohexylethyl crotonate;esters of cycloaliphatic carboxylic acids, e.g. allyl3-cyclohexylpropionate; allyl cyclohexyloxyacetate; cis- andtrans-methyl dihydrojasmonate; cis- and trans-methyl jasmonate; methyl2-hexyl-3-oxocyclopentanecarboxylate; ethyl2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; ethyl2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; ethyl2-methyl-1,3-dioxolan-2-acetate;

araliphatic alcohols, e.g. benzyl alcohol; 1-phenylethyl alcohol;2-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol;2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol;2,2-dimethyl-3-(3-methylphenyl)propanol; 1,1-dimethyl-2-phenylethylalcohol; 1,1-dimethyl-3-phenylpropanol;1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol;3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzylalcohol; 1-(4-isopropylphenyl)ethanol;

esters of araliphatic alcohols and aliphatic carboxylic acids, e.g.benzyl acetate; benzyl propionate; benzyl isobutyrate; benzylisovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate;2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethylacetate; alpha-trichloromethylbenzyl acetate;alpha,alpha-dimethylphenylethyl acetate; alpha,alpha-dimethylphenylethylbutyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzylacetate;

araliphatic ethers, e.g. 2-phenylethyl methyl ether; 2-phenylethylisoamyl ether; 2-phenylethyl 1-ethoxyethyl ether; phenylacetaldehydedimethyl acetal; phenylacetaldehyde diethyl acetal; hydratropaldehydedimethyl acetal; phenylacetaldehyde glyceryl acetal;2,4,6-trimethyl-4-phenyl-1,3-dioxane;4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxin;4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin;

aromatic and araliphatic aldehydes, e.g. benzaldehyde;phenylacetaldehyde; 3-phenylpropanal; hydratropaldehyde;4-methylbenzaldehyde; 4-methylphenylacetaldehyde;3-(4-ethylphenyl)-2,2-dimethylpropanal;2-methyl-3-(4-isopropylphenyl)propanal;2-methyl-3-(4-tert-butylphenyl)propanal;2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert-butylphenyl)-propanal;cinnamaldehyde; alpha-butylcinnamaldehyde; alpha-amylcinnamaldehyde;alpha-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal;4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde;4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde;3,4-dimethoxybenzaldehyde; 2-methyl-3-(4-methoxyphenyl)propanal;2-methyl-3-(4-methylenedioxyphenyl)-propanal;

aromatic and araliphatic ketones, e.g. acetophenone;4-methylacetophenone; 4-methoxyacetophenone;4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone;4-(4-hydroxyphenyl)-2-butanone; 1-(2-naphthalenyl)ethanone;2-benzofuranylethanone; 3-methyl-2-benzofuranylethanone; benzophenone;1,1,2,3,3,6-hexamethyl-5-indanyl methyl ketone;6-tert-butyl-1,1-dimethyl-4-indanyl methyl ketone;1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone;5′,6′,7′,8′-tetrahydro-3′,5′,5′,6′,8′,8′-hexamethyl-2-acetonaphthone;

aromatic and araliphatic carboxylic acids and their esters, e.g. benzoicacid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexylbenzoate; benzyl benzoate; methylphenyl acetate; ethylphenyl acetate;geranylphenyl acetate; phenylethylphenyl acetate; methyl cinnamate;ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamylcinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl salicylate;hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate;benzyl salicylate; phenylethyl salicylate; methyl2,4-dihydroxy-3,6-dimethylbenzoate; ethyl 3-phenylglycidate; ethyl3-methyl-3-phenylglycidate;

aromatic nitrogen-containing compounds, e.g.2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene;3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamic acidnitrile; 3-methyl-5-phenyl-2-pentenoic acid nitrile;3-methyl-5-phenylpentanoic acid nitrile; methyl anthranilate; methylN-methyl-anthranilate; Schiff bases of methyl anthranilate with7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert-butylphenyl)propanalor 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6-isopropylquinoline;6-isobutylquinoline; 6-sec-butylquinoline; 2-(3-phenylpropyl)pyridine;indole; skatole; 2-methoxy-3-isopropylpyrazine;2-isobutyl-3-methoxypyrazine;

phenols, phenyl ethers and phenyl esters, e.g. estragole; anethole;eugenol; eugenyl methyl ether; isoeugenol; isoeugenyl methyl ether;thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether;beta-naphthyl ethyl ether; beta-naphthyl isobutyl ether;1,4-dimethoxybenzene; eugenyl acetate; 2-methoxy-4-methylphenol;2-ethoxy-5-(1-propenyl)-phenol; p-cresylphenyl acetate;

heterocyclic compounds, e.g. 2,5-dimethyl-4-hydroxy-2H-furan-3-one;2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one;3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;

lactones, e.g. 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide;1,4-decanolide; 8-decen-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide;1,5-decanolide; 1,5-dodecanolide; 4-methyl-1,4-decanolide;1,15-pentadecanolide; cis- and trans-11-pentadecen-1,15-olide; cis- andtrans-12-pentadecen-1,15-olide; 1,16-hexadecanolide;9-hexadecen-1,16-olide; 10-oxa-1,16-hexadecanolide;11-oxa-1,16-hexadecanolide; 12-oxa-1,16-hexadecanolide; ethylene1,12-dodecanedioate; ethylene 1,13-tridecanedioate; coumarin;2,3-dihydrocoumarin*; octahydrocoumarin*.

Note: The substances marked with an * in the above list have a coconutodour and therefore are only used in particular cases in combinationwith 4,8-dimethyl-7-nonen-2-one or 4,8-dimethylnonan-2-one. Compoundswhich have a sensitizing/allergizing effect and whose use is thereforeonly advantageous in particular cases have again been underlined.

Each combinations are preferred and which are less advantageous can beseen especially from the above remarks. Accordingly, combination withrose fragrances is particularly preferred, whereas combination withallergenic fragrances is less advantageous (even if these are themselvesrose fragrances, e.g. citronellol and geraniol).

The amount of the two ketones according to the invention used in perfumecompositions is 0.01 to 99.9 wt. %, preferably 0.1 to 90% andparticularly preferably 0.5 to 70%, based in each case on the totalperfume oil composition.

Perfume oils containing 4,8-dimethyl-7-nonen-2-one and4,8-dimethylnonan-2-one can be used for perfume formulations in liquidform, either undiluted or diluted with a solvent. Examples of suitablesolvents for this purpose are ethanol, isopropanol, diethylene glycolmonoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol,dipropylene glycol, diethyl phthalate, triethyl citrate, isopropylmyristate, etc.

Perfume oils containing the two ketones according to the invention canalso be adsorbed on a carrier to ensure both a fine distribution of thefragrances in the product and a controlled release when used. Suchcarriers can be porous inorganic materials, such as light sulfate,silica gels, zeolites, gypsums, clays, clay granules, gas concrete,etc., or organic materials, such as woods, cellulose-based substances,sugars or plastics like PVC, polyvinyl acetates or polyurethanes.

Perfume oils containing the two ketones according to the invention canalso be microencapsulated or spray-dried or in the form of inclusioncomplexes or extrusion products, and can be added in this form to theproduct to be perfumed.

Optionally the properties of the perfume oils modified in this way canbe further optimized, in respect of a more specific perfume release, bycoating with suitable materials; waxy plastics, e.g. polyvinyl alcohol,are preferably used for this purpose.

Microencapsulation of the perfume oils can be effected for example bythe so-called coacervation process with the aid of capsule materialsmade e.g. of polyurethane-like substances or soft gelatin. Spray-driedperfume oils can be prepared for example by spray drying an emulsion ordispersion containing the perfume oil, it being possible for modifiedstarches, proteins, dextrin and vegetable gums to be used as carriers.Inclusion complexes can be prepared for example by introducingdispersions of the perfume oil and cyclodextrins or urea derivativesinto a suitable solvent, e.g. water. Extrusion products can be obtainedby melting the perfume oils with a suitable waxy substance and byextrusion with subsequent solidification, optionally in a suitablesolvent, e.g. isopropanol.

Perfume oils containing the two ketones according to the invention canbe used in concentrated form, in solution or in a modified formdescribed above for the preparation of e.g. perfume extracts, eaux deparfum, eaux de toilette, after-shave lotions, eaux de Cologne,pre-shave products, splash colognes and perfumed refreshing tissues, andfor the perfuming of acidic, alkaline and neutral cleaning products,e.g. floor cleaners, window cleaners, dishwasher detergent, bath andsanitaryware cleaners, scouring cream, solid and liquid WC cleaners,carpet cleaning powders and foams, fabric fresheners, ironing aids,liquid detergents, powder detergents, fabric preconditioners such asbleach, soaker and stain removers, fabric softeners, washing soaps,washing tablets, disinfectants, surface disinfectants, air purifiers inliquid or gel form or applied to a solid carrier, aerosol sprays, waxesand polishes, such as furniture polishes, floor waxes and shoe polishes,body care products, e.g. solid and liquid soaps, shower gels, shampoos,shaving soaps, shaving foams, bath oils, cosmetic emulsions of theoil-in-water, water-in-oil and water-in-oil-in-water type, such as skincreams and lotions, face creams and lotions, sun creams and lotions,after-sun creams and lotions, hand creams and lotions, foot creams andlotions, depilatory creams and lotions, after-shave creams and lotions,tanning creams and lotions, hair care products, e.g. hair sprays, hairgels, strengthening hair lotions, hair rinses, permanent andsemipermanent hair dyes, hair styling products, such as cold waving andstraightening products, hair tonics, hair creams and lotions, deodorantsand anti-perspirants, e.g. armpit sprays, roll-ons, deodorant sticks anddeodorant creams, decorative cosmetic products, e.g. eye shadows, nailvarnishes, make-ups, lipsticks and mascara, and candles, lamp oils,incense sticks, insecticides, repellents and propellants.

The invention is illustrated in greater detail below by means ofExamples:

EXAMPLE 1 Preparation of 4,8-dimethyl-7-nonen-2-one by the hydrogenationof 4,8-dimethyl-3,7-nonadien-2-one

116.2 g of 4,8-dimethyl-3,7-nonadien-2-one (cf. DE 2256347 C3, DE19961030 A1) are dissolved in 150 ml of ethyl acetate and hydrogenatedin the presence of 7 g of Raney nickel in a 1 l steel autoclave at atemperature of 30 to 35° C. and a hydrogen pressure of 30 bar. Whenapprox. 1.2 mol equivalents of hydrogen have been taken up, all the4,8-dimethyl-3,7-nonadien-2-one has been converted. The hydrogenation isstopped, the catalyst is filtered off, the solvent is distilled off andthe 4,8-dimethyl-7-nonen-2-one is isolated in pure form from theresulting crude product by fractionation in a Spaltrohr® column(manufactured by Fischer Labor—und Verfahrenstechnik GmbH). Yield 90 g(77% of theory), b.p. 63° C. at 0.2 mbar.

Odour: radiantly rose-like, natural, reminiscent of tea roses,citronellol-like, geranium-like

EXAMPLE 2 Preparation of 4,8-dimethylnonan-2-one by the hydrogenation of4,8-dimethyl-3,7-nonadien-2-one

In a reaction set-up such as that described in Example 1, thehydrogenation was carried out at a pressure of 50 bar until 2 molequivalents of hydrogen had been taken up. After the work-up,4,8-dimethylnonan-2-one was obtained in pure form from the crude productby fractionation in a Spaltrohr® column. Yield 107 g (90% of theory),b.p. 58° C. at 0.4 mbar.

Odour: fresh, rose-like, somewhat citric-lemony, citronellol-like

EXAMPLE 3 Preparation of a Perfume with a Rose-Like Scent using4,8-dimethyl-7-nonen-2-one and 4,8-dimethylnonan-2-one

Firstly the following are mixed: Fragrance Parts by weight 10-Undecenal2 Datilat H&R (1-cyclohexylethyl crotonate) 15 9-Decenol 1 Eugenol 5Guaiacum wood oil 7 Indoflor H&R (2,4-dimethyl-5,6-indeno-1,3- dioxane)2 alpha-Ionone 20 beta-Ionone 7 Cyclohexadecanone 17 Phenylacetaldehyde10 percent in dipropylene glycol 7 Pyroprunat H&R (2cyclopentylcyclopentyl crotonate) 10 Rose oxide 10 percent indipropylene glycol 7 100

The addition of 125 parts by weight of 4,8-dimethyl-7-nonen-2-one and125 parts by weight of 4,8-dimethylnonan-2-one gives a perfume oil witha fresh, radiant and modern rose note, which is outstandingly suitablefor perfuming cleaners, fabric softeners, washing powders, airpurifiers, soaps, shampoos, bath additives, skin creams, body lotions,deodorants and other cosmetics.

EXAMPLE 4 Preparation of a Perfume with a Rose-Like Scent using4,8-dimethyl-7-nonen-2-one

The following are mixed: Fragrance Parts by weight 10-Undecenal 2Datilat H&R (1-cyclohexylethyl crotonate) 15 9-Decenol 1 Eugenol 5Guaiacum wood oil 7 Indoflor H&R (2,4-dimethyl-5,6-indeno-1,3- dioxane)2 alpha-Ionone 20 beta-Ionone 7 Cyclohexadecanone 17 Phenylacetaldehyde10 percent in dipropylene glycol 7 Pyroprunat H&R(2-cyclopentylcyclopentyl crotonate) 10 Rose oxide 10 percent indipropylene glycol 7 100

The addition of 50 parts by weight of 4,8-dimethyl-7-nonen-2-one gives aperfume oil with an extremely natural tea rose-like olfactory note,which is likewise outstandingly suitable for perfuming cleaners, fabricsofteners, washing powders, air purifiers, soaps, shampoos, bathadditives, skin creams, body lotions, deodorants and other cosmetics.

1. A method of imparting a rose odour to a composition that is notaccompanied by a coconut olfactory note by adding to said composition4,8-dimethyl-7-nonen-2-one, 4,8-dimethylnonan-2-one or a mixture ofthese compounds.
 2. A method according to claim 1 wherein saidcomposition is a perfume.
 3. A method of imparting a rose odour to acomposition wherein 4,8-dimethylnonan-2-one is added to said compositionas a fragrance.
 4. Perfume composition with a rose odour, comprising anorganoleptically effective amount of 4,8-dimethyl-7-nonen-2-one,4,8-dimethylnonan-2-one or a mixture of these compounds, and at leastone other fragrance.
 5. Perfume composition according to claim 4 whereinthe other fragrance is selected from the group comprising: geranylformate; geranyl acetate; geranyl propionate; geranyl isobutyrate;geranyl butyrate; geranyl isovalerate; geranyl tiglate; geranylbenzoate; citronellyl formate; citronellyl acetate; citronellylpropionate; citronellyl isobutyrate; citronellyl butyrate; citronellylisovalerate; citronellyl tiglate; citronellyl benzoate; phenylethylalcohol; phenylacetaldehyde; phenylacetaldehyde dimethyl acetal;phenylethyl formate; phenylethyl acetate; phenylethyl propionate;phenylethyl isobutyrate; phenylethyl butyrate; phenylethyl pivalate;phenylethyl isovalerate; phenylethyl 2-ethylbutyrate; phenylethyltiglate; phenylethyl benzoate; phenylethylphenyl acetate; 2-phenoxyethylisobutyrate; geranyl methyl ether; rose oxide; phenylethyl methyl ether;phenylethyl ethyl ether; phenylethyl isoamyl ether; 2-methoxybenzylethyl ether; α-trichloromethylbenzyl acetate;α,3,3-trimethylcyclohexanemethyl acetate;2,4,6-trimethyl-3-cyclohexenemethanol; 2-ethylhexanoic acidN,N-diethylamide; 3,7-dimethyloctanol; geranylacetone; linalool;3,7-dimethyl-1,6-nonadien-3-ol; nerolidol; farnesol; 9-decenol;9-decenyl acetate; decanal; 10-undecanal; 10-undecenol;citronellyloxyacetaldehyde; 3,7-dimethyloctanylacetaldehyde;2-methyl-5-phenylpentanol; 2-methyl-5-phenylpentanal;3-methyl-5-phenylpentanol; benzophenone; diphenyl ether;diphenylmethane; α-damascone; β-damascone; δ-damascone; γ-damascone;β-damascenone; 1-(2,4,4-trimethyl-2-cyclohexenyl)-2-buten-1-one; roseoil; rose absolute; geranium oil; palmarosa oil; lemon oil; patchoulioil; clove oil; ylang-ylang oil; jasmine absolute; ethyl2,3,6-trimethylcyclohexyl carbonate; hexanal; heptanal; octanal;nonanal; hexanol; heptanol; octanol; nonanol; decanol; undecanol;dodecanol; hexyl acetate; heptyl acetate; octyl acetate; nonyl acetate;decyl acetate; undecyl acetate; dodecyl acetate; benzyl acetate; benzylbutyrate; benzyl benzoate; methylphenyl acetate; ethylphenyl acetate;alpha-terpineol;4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin;4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxin; ethyl2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; ethyl2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; ethyl safranate; methyl6,6-dimethyl-2-methylenecyclohexanecarboxylate; eugenol; isoeugenol;lavender oil; guaiacum wood oil; alpha-ionone; beta-ionone; cinnamylalcohol; 3-phenylpropanol; cinnamyl acetate; 3-phenylpropyl acetate;alpha-irone; cis-3-hexenol; cis-3-hexenyl acetate; cis-3-hexenylisobutyrate; vanillin; ethylvanillin; heliotropin; coumarin; ambrinol;indole; 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan;5-cyclohexadecen-1-one;6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone;8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone;cyclohexadecanone.
 6. Perfume composition according to claim 4 whereinthe other fragrance is selected from the group of fragrances with a roseodour comprising: geranyl formate; geranyl acetate; geranyl propionate;geranyl isobutyrate; geranyl butyrate; geranyl isovalerate; geranyltiglate; geranyl benzoate; citronellyl formate; citronellyl acetate;citronellyl propionate; citronellyl isobutyrate; citronellyl butyrate;citronellyl isovalerate; citronellyl tiglate; citronellyl benzoate;phenylethyl alcohol; phenylacetaldehyde; phenylacetaldehyde dimethylacetal; phenylethyl formate; phenylethyl acetate; phenylethylpropionate; phenylethyl isobutyrate; phenylethyl butyrate; phenylethylpivalate; phenylethyl isovalerate; phenylethyl 2-ethylbutyrate;phenylethyl tiglate; phenylethyl benzoate; phenylethylphenyl acetate;2-phenoxyethyl isobutyrate; geranyl methyl ether; rose oxide;phenylethyl methyl ether; phenylethyl ethyl ether; phenylethyl isoamylether; 2-methoxybenzyl ethyl ether; α-trichloromethylbenzyl acetate;α,3,3-trimethylcyclohexanemethyl acetate;2,4,6-trimethyl-3-cyclohexenemethanol; 2-ethylhexanoic acidN,N-diethylamide; 3,7-dimethyloctanol; geranylacetone; linalool;3,7-dimethyl-1,6-nonadien-3-ol; nerolidol; farnesol; 9-decenol;9-decenyl acetate; decanal; 10-undecanal; 10-undecenol;citronellyloxyacetaldehyde; 3,7-dimethyloctanylacetaldehyde;2-methyl-5-phenylpentanol; 2-methyl-5-phenylpentanal;3-methyl-5-phenylpentanol; benzophenone; diphenyl ether;diphenylmethane; α-damascone; β-damascone; δ-damascone; γ-damascone; 62-damascenone; 1-(2,4,4-trimethyl-2-cyclohexenyl)-2-buten- 1-one; roseoil; rose absolute; geranium oil.
 7. Perfume composition according toone of claim 4, characterized in that it does not contain fragrancesselected from the group comprising: amylcinnamaldehyde, amylcinnamylalcohol, anisyl alcohol, benzaldehyde, benzyl alcohol, benzyl benzoate,benzyl cinnamate, benzyl salicylate, citral, citronellol, coumarin,eugenol, farnesol, geraniol, hexylcinnamaldehyde, hydroxycitronellal,isoeugenol, lilial, limonene, linalool, lyral, methyl heptynecarbonate,methylionone, methyl octynecarbonate, cinnamaldehyde, cinnamyl alcohol,and natural products containing these compounds in an effective amount.8. Perfume composition according to one of claim 4, containing4,8-dimethyl-7-nonen-2-one, 4,8-dimethylnonan-2-one or a mixture ofthese compounds in an amount which modifies the olfactory properties ofa mixture of the other constituents of the perfume composition in thedirection of freshness and/or radiance.
 9. Perfume composition accordingto one of claim 4, characterized in that the proportion of4,8-dimethyl-7-nonen-2-one, 4,8-dimethylnonan-2-one or a mixture ofthese compounds ranges from 0.1 to 90 wt. %, preferably from 0.5 to 70wt. %, based on the total weight of the perfume composition. 10.Perfumed product comprising a perfume composition according to claim 4.11. Process for producing a rose odour or strengthening the rose odourof a perfume composition or perfumed product, the rose odour not beingaccompanied by a coconut olfactory note, characterized in that asensorially effective amount of 4,8-dimethyl-7-nonen-2-one,4,8-dimethylnonan-2-one or a mixture of these compounds is mixed withthe other constituents of the perfume composition or added to theproduct.